Discovery of Pyrido[1,2-a]pyrimidinone Mesoionic Compounds Incorporating a Dithioacetal Moiety as Novel Potential Insecticidal Agents

Abstract

A series of novel mesoionic pyrido­[1,2-a]­pyrimidinone compounds incorporating a dithioacetal skeleton were designed and synthesized for use as insecticidal agents. The biological activity of the title compounds indicated good to excellent insecticidal activities against bean aphids (Aphis craccivora) and white-backed planthoppers (Sogatella furcifera). Compound 34 showed excellent insecticidal activity against bean aphids (A. craccivora) with an LC50 value of 2.80 μg/mL, exceeding the insecticidal activity of trifluoropyrimidine (LC50 = 4.20 μg/mL). Proteomics and molecular docking results indicated that compound 34 could act on nicotinic acetylcholine receptors. This study provides support for the application of mesoionic pyrido­[1,2-a]­pyrimidinone compounds containing dithioacetal as novel insecticidal agents.

Pyrido [1,2-a] Pyrimidinone Mesoionic Compounds Containing Vanillin Moiety: Design, Synthesis, Antibacterial Activity, and Mechanism

“…Targeted pests of mesoionic compounds with novel structures − and unique mechanisms of action are mainly Hemiptera and Lepidoptera. − As nicotinic acetylcholine receptor (nAChR) inhibitors, − mesoionic compounds have no cross-resistance with traditional pesticides. We have previously expanded the biological activity spectrum of mesoionic compounds and discovered a mesoionic compound “ A11 ” with antibacterial activity, for the first time. , Compound “ A11 ” bears vanillin structural units that exhibited antibacterial and antiviral − activities.…”

“…To the best of our knowledge, the application of mesoionic compounds as insecticides or their modes of action has been widely explored. ,, However, there are only a few examples concerning antibacterial mechanisms of mesoionic compounds at present . In light of this, the work described here is primarily focused on designing, synthesizing, and determining the antibacterial activity and the mechanism of mesoionic compounds.…”

First Discovery of Imidazo[1,2-a]pyridine Mesoionic Compounds Incorporating a Sulfonamide Moiety as Antiviral Agents

“…Our research group is committed to the development of novel pesticides with excellent activities and low toxicities to non-target organisms and new action modes. In our previous studies, a broad range of mesoionic compounds with good insecticidal − and antibacterial , properties were designed and synthesized. Furthermore, we found that sulfonamide derivatives showed good antiviral activities. − In this case, we hope that introducing a sulfonamide moiety into mesoionic compounds might favor the expected antiviral activity.…”

Discovery of Mesoionic Derivatives Containing a Dithioacetal Skeleton as Novel Potential Antibacterial Agents and Mechanism Research

“…In our previous work, numerous mesoionic derivatives were prepared, and an activity assay showed that some target compounds exhibited antibacterial , and insecticidal activities. − Furthermore, mesoionic compounds have unique physical and chemical properties , and multiple biological activities, such as antifungal, antibacterial, , insecticidal, − and other extensive biological activities. Therefore, mesoionic compounds have broad market value and application prospects in agricultural development.…”